7472-67-5Relevant articles and documents
A general synthesis of 2-alkoxy-2-phenylpropanoic acids
Monk, Keith A.,Duncan, Nathan C.,Bauch, Eric A.,Garner, Charles M.
, p. 8605 - 8609 (2008/12/21)
A preparation of a variety of 2-alkoxy-2-phenylpropanoic acids in two steps is described. Epoxidation of α-methylstyrene with mCPBA in methanol or primary alcohol solvents proceeded with an acid-catalyzed in situ ring opening reaction to give the corresponding 2-alkoxy-2-phenyl-1-propanols in 28-91% yield. Lower yields were realized with secondary (22-58%) and tertiary (14%) alcohols. These alcohols were cleanly oxidized to the corresponding carboxylic acids using a mild Heyns' oxidation (O2, Pt/C) in generally good to excellent yields (25-92%). The derived (S)-α-methylbenzylamide diastereomers are nearly all well separated by capillary GC, and the use of this method to determine the enantiomeric purity of brucine-resolved 2-methoxy-2-phenylpropanoic acid was demonstrated.
Conformational analysis of MαNP esters, powerful chiral resolution and 1H NMR anisotropy tools - aromatic geometry and solvent effects on Δδ values
Kasai, Yusuke,Sugio, Akinori,Sekiguchi, Satoshi,Kuwahara, Shunsuke,Matsumoto, Takatoshi,Watanabe, Masataka,Ichikawa, Akio,Harada, Nobuyuki
, p. 1811 - 1826 (2008/02/08)
The MαNP acid method is very powerful for the preparation of enantiopure alcohols by resolution and the simultaneous determination of their absolute configurations by the 1H NMR anisotropy effect, where the syn-syn conformation is taken as the
Regioselective synthesis of optically active (pyrazolyl)pyridines with adjacent quaternary carbon stereocenter: Chiral N,N-donating ligands
Kowalczyk, Rafa?,Skarzewski, Jacek
, p. 623 - 628 (2007/10/03)
Novel optically active 2-(pyrazol-1-yl)pyridines have been prepared using resolved the O-methyl ether of atrolactic acid as a source of the adjacent quaternary carbon stereocenter. Different regioisomers were formed selectively in the reaction of 2-hydraz
A convenient one-pot synthesis of quaternary α-methoxy- and α- hydroxycarboxylic acids
Yabuuchi, Tetsuya,Kusumi, Takenori
, p. 684 - 686 (2007/10/03)
Several α-methoxy- and α-hydroxycarboxylic acids have been synthesized by a new one-pot synthesis using ketones, tribromomethane, and potassium hydroxide in methanol and water, respectively, in good yields.
ENANTIOSELECTIVE α-SELENENYLATION OF 2-PHENYLPROPANAL
Paulmier, Claude,Outurquin, Francis,Plaquevent, Jean-Cristophe
, p. 5889 - 5892 (2007/10/02)
The parameters (media, temperature, structures of reactants) relative to the enantioselective α-selenenylation of 2-phenylpropanal with chiral areneselenenamides have been studied.Enantiomeric excesses as high as 60percent have been observed.Recrystallization yielded an α-seleno-aldehyde in an optically pure form.
The Effect of Lewis Acid and Solvent on Concerted 1,2-Acyl Migration
Bach, Robert D.,Domagala, John M.
, p. 4181 - 4188 (2007/10/02)
Lewis acid catalyzed 1,2-benzoyl migration in (E)- and (Z)-1,3-diphenyl-2-buten-1-on oxides (dypnone oxides) is a concerted process that occurs with inversion of configuration at the migration terminus when nonpolar solvents are employed.In methanol solve